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Updated: Sep 22, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Light-Induced Step-Growth Polymerization of AB-Type Photo-Monomers at Ambient Temperature
Silvana Hurrle1, Anja S Goldmann2,1, Hartmut Gliemann3
1Macromolecular Architectures, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstraße 18, 76128 Karlsruhe, Germany.
Abstract:
We introduce two AB-type monomers able to undergo a facile catalyst-free photoinduced polycycloaddition of photocaged dienes, enabling rapid Diels-Alder ligations under UV-irradiation (λmax = 350 nm) at ambient temperature, closely adhering to Carother's equation established by a careful kinetic study (17800 g mol-1 < Mw < 24700 g mol-1). The resulting macromolecules were in-depth analyzed via size exclusion chromatography (SEC) and nuclear magnetic resonance (NMR) spectroscopy. Additionally, SEC hyphenated to high resolution-electrospray ionization-mass spectrometry (HR-ESI-MS) enabled the careful mapping of the end group structure of the generated polymers. Furthermore, we demonstrate that both monomer systems can be readily copolymerized. The study thus demonstrates that Diels-Alder ligation resting upon photocaged dienes is a powerful tool for accessing step-growth polymers.
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